Computation and Simulation Unit, Analytical Discipline & Centralized Instrument Facility, and Academy of Scientific and Innovative Research, CSIR-Central Salt and Marine Chemicals Research Institute , Bhavnagar, Gujarat 364002, India.
Org Lett. 2014 Apr 18;16(8):2100-3. doi: 10.1021/ol500461s. Epub 2014 Apr 3.
DFT (M06-L) calculations on the transition state for the 1,3-dipolar cycloadditions between substituted vinyl sulfones with sugar azide have been reported in conjunction with new experimental results, and the origin of reversal of regioselectivity has been revealed using a distortion/interaction model. This study provides the scientific justification for combining organic azides with two different types of vinyl sulfones for the preparation of 1,5-disubstituted 1,2,3-triazoles and 1,4-disubstituted triazolyl esters under metal-free conditions.
已报道了取代乙烯砜与糖叠氮化物的 1,3-偶极环加成反应过渡态的 DFT（M06-L）计算，同时结合了新的实验结果，并使用扭曲/相互作用模型揭示了区域选择性反转的起源。该研究为在无金属条件下，将有机叠氮化物与两种不同类型的乙烯砜结合，用于制备 1,5-二取代 1,2,3-三唑和 1,4-二取代三唑基酯提供了科学依据。
